How to host an epic WORK SESSION at your next corporate retreat

If you know anything about Offsite and our mission, you know we’re all about having a good time, but retreats can also be a great way to amplify team productivity.

And the best way to do this is through work sessions. So while many of our articles are about fun, this article is about getting down to business.

Disclaimer: We’ll still be talking about how to add a fun flare to your work. After all, it wouldn’t be Offsite without a bit of spice. 

BENEFITS

WHAT’S IN IT FOR ME?

Typically people don’t like when you ask what’s in it for you, but hey, with retreats where there are countless benefits, we love that questions. And we’re not above a humble little brag. ;)

We already know there are proven benefits to hosting a company retreat, especially one of epic proportions, but let’s run it back.

A Team that Retreats Together Stays Together

It's science, and you can't argue with science.

But for the skeptics out there, yeah, we're talking to you, here are some stats to calm your nerves:

  • Between team bonding, destressing, and travel perks, offsites and company retreats can help combat loneliness, reducing life expectancy by a staggering 70% (Forbes).

  • Let's be honest; corporate retreats are like a vacation you put on the company card. 83% of workers agree, seeing corporate travel as a perk of their job (Stratos). (Don't worry, the company also reaps a ton of benefits!) And when it comes to traveling, even thinking about plans can increase happiness by 18%(Airbnb).

  • 73% of remote employees miss socializing with their teams (Indeed).

  • According to the Global Business Travel Association, most workers believe business travel impacts their general sense of job satisfaction. In North America, 79% of participants agreed with this statement, rising to 83% in Europe and 96% in Asia (GBTA).

You Actually Save Money

And since we're already talking numbers, we'll let them speak:

  • Every dollar spent on corporate travel generates $12.50 in returns (TravelPerk).

  • Organizations with limited corporate travel could lose up to 28% of current business (Stratos).

  • Replacing a previous hire can cost a business 30% of the salary of an entry-level position, all the way up to 400% of an executive's salary. With retention rates rising at retreats, you can't afford not to have them (TLNT).

You Get Sh*t Done

And of course, the reason you clicked on this article, with in-person brainstorming sessions, speaker sessions, and workshops, you can get a lot done at retreats, especially when combined with company kickoffs.

  • 4% of employees shared that they have had their most creative ideas on business trips. This figure increases to 53% for corporate travelers between the ages of 16 and 24 (TravelPerk).

  • While the world may have gone remote, 81% of millennial employees think they work more effectively when they have face time with their coworkers (Forbes).

WORK SPACE

If you’ve read our venue highlights for company retreats in Lake Tahoe, you probably notice we always mention their workspaces. Why? Because you need to have the perfect place to get sh*t done, and that ideal place depends on the team. Who knows, maybe your team is the type to “crunch the numbers” poolside, but if you prefer a more traditional style, make sure your venue has a suitable workspace, or consider renting one out from Peerspace.

The goals of your employee retreat will dictate if work sessions should be sculpted into the agenda. Our general rule of thumb is to have at least one area where people can get together to get work done. Then, if you’re like us, we want that workspace to be an inspiring place for people to meet.

Things to consider when looking at a venue’s workspace:

  • What are the capacity limits?

  • Does the workspace fit my purpose? (ie. Smaller meeting rooms with desk space for brainstorming sessions and larger conference halls for speaker sessions)

  • Is there access to high-speed wifi?

  • Do they supply projection and presentation equipment if you need it?

Whatever your needs, work with your venue to negotiate inclusion for a workspace inside of your quote. For smaller teams looking to get more work done, we use sites like Breather and Splacer.

Having a hard time picking the perfect workspace, hand it over to us. We do all the heavy lifting, from finding a stunning venue to satisfying your late-night pizza cravings.

AGENDA

While including breaks between work sessions are essential in preventing burnout, you also need to ensure you're scheduling the work time efficiently. Blending sessions, speakers, and ad-hoc syncs will help to break up the work sessions and prevent them from feeling like another day in the office. Consider adopting Zapier's method of designating themes for each workday. This allows each day to be productive while preventing it from feeling too repetitive. Some themes to choose from are marketing, team-building, and product management. 


The single-handed most important step of retreat planning is goal-setting. Seriously, without a purpose, you can't have a plan.

These goals apply to every part of the retreat, including work sessions. So before we can get to the good part, you must answer this simple question: why are we here?

Two common goals we hear every day for our clients when we ask, "why are you investing in this company retreat for your team are:"

A) Get everyone aligned on the mission and vision of our company

B) Build real human connections between colleagues.

While we're all about checking off your to-do lists, we believe that the biggest goal of work sessions is to inspire the collective team on the company's mission and vision.

We want everyone to feel like they are all-in on the mission when they fly home. We want everyone to leave with that "hey, I'm on this rocket ship with this community of people" feeling, and we're going to show you how to do just that.

THE THREE THEMES

To do this, we like to have three meetings focused on three very important themes: past, present, and future. Buckle in because we're about to Scrooge this joint (but you know, in less of a bitter way and more of a baller way).

Here's the meeting Structure:

Where Did We Come From?

I want to start by saying if you began to sing cotton-eyed Joe, please use this as an intermission to book us as your retreat planner because you’re our type of people.

Anyways, back to business.

We recommend having this discussion in a really casual way. So we’re talking a first-night happy hour or over coffee.

Have leadership get up, props if you stand on a table, and share some anecdotal stories about where the company has come from. What we want to do is humanize leadership and ethos of this fast-growing company.

If you can help the team see that this was, at one point, just an idea. It took an incredible amount of hustle and build to get it to where we are today; you’ll build trust.

Where are we Today? 

This is a great session to use an all-hands meeting for. Build a PowerPoint outlining where the business is today. It’s important to be vulnerable, both from a leadership perspective and on behalf of the business as a whole. We know it’s not all roses. Make a point to outline the good, bad, and ugly.

One way to do this is to outline a competitive analysis for the business. You don’t have to go into deep, deep detail, but it shows that we have money and we have holes to fill in the company.

Where Did We Go?

Let’s sell the vision now. You want to create the feeling that “if we can all execute on our strategy, the big carrot is out there for us.”

Remember, we want people to leave feeling like they are a part of the biggest opportunity in your space!

BREAKOUTS

Now that we have told this story of where we came from, where we are today, and where we have the opportunity to go, let’s figure out how we will get there.

1) Split the teams randomly and have them tackle different elements of your growth plan.

This can be tactical strategies, or it can just be a thought experiment with small teams getting together and poking holes in the strategy around where you are going.

2) Split into teams by function.

This is a fantastic time to let various team functions work together. Team leads can develop a conversation or project for the group to tackle, or they can just decide the team will benefit from working independently but in the same room.

THE END

As we said, it’s so incredibly important to humanize your leadership. And one of our favorite ways to do this is through surveys. Send out a survey to the entire team. Ask them if you could ask one question to leadership entirely anonymously; what would it be?

Comb through those questions submitted and cherry-pick 7-12 of them. Give them to leadership before the event so they can be aligned on the answers to these questions. Set up a “Fireside Chat” environment and have someone from your team ask the questions to leadership.

This is how you show your staff that you hear them, that they matter.

And bam! That’s how you have a productive retreat of epic proportions— at least how to host a work session. Ready to start the next sections? Check out our retreat guides

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